Try Harder Next Time
by x stickers
Summary: Silk is ruthless, spoiled, and always ready to cut someones throat- demon or not. She is selfish and only cares about her personal goals.. until she meets the Winchester boys. Suddenly, Silk finds herself sticking her neck out for these brothers she hardly even knows, and even worst.. she finds herself caring! These boys are really cursed, indeed. Dean/OC Romance,Sam/OC Friendship


_'Loving you, is easy 'cause your beautiful..'_

The room was dimly lit with vanilla scented candles, the smell giving an intense romantic aroma. There was a soft moan over the sound of the radio followed by a deep male chuckle. Tangled in satin sheets, the woman and the man shared a kiss before he dipped the strawberry fruit back into her mouth, allowing her to take a bite.

"I have to say.. this date went better then I expected, _Marissa_."

_'Making love with you, is all I wanna do..'_

"Mmmhmm.." The brunette purred against his neck as his lips traveled to her ear, whispering to her sweetly.

She pulled her head back to cast him a lazy smile, "But the date isn't over yet, James-"

_Ring, Ring, Ring._

Pause.

_Ring, ring, ring._

A low groan rumbled from the back of her throat as she pulled away from James without hesitation, hand shoving its way into her purse to fish out the source of her dismay. The woman pulled out her phone, eyes widening at the name that flashed across her caller I.D.

Call from: _D._

She flipped it open immediately, ignoring the sound of disbelief that came from James next to her.

"Dean?" She answered.

**"Silk? I gotta say, I'm mildly surprised you even gave me the right number."**

Silk sat up from the bed, the maroon sheet slipping down from her body to reveal the black lingerie bra she was dressed down to, and swung her legs over the side of the bed to put on her slippers. James pawed at her arm gingerly, a pout forming his boyish features as he gripped her wrist. "Marissa, come back to bed-"

"You, shut up." Silk snapped at James before he could start _begging_- _God _she hated beggars. She snatched her wrist from him with ease and stood up to tie her royal blue robe around her body, making herself decent once again. Silk returned her attention back to her phone conversation, "Well, I have to say, Dean, I'm equally surprised you called."

I mean, the first time they had met, it wasn't exactly on the best terms. In fact, Silk can remember punching a certain elder Winchester in the nose after both he and his brother held her hostage under the false impression that she was a demon. Of course, that was all water under the bridge now.

"**Oh God-**-," Dean groaned in disgust from the other side of the phone as he heard Minnie Riperton's 'Loving You' in the background, as well as James' voice. "**If your **_**busy**_**, I can call back later. Or we can just pretend I never called in the first place. Either is starting to sound good right now.**"

Silk laughed whole-heartidly at Dean's obvious disgust in her, twirling the rope of her robe around her finger as she leaned back into her chair. She crossed her legs and adjusted the phone against her ear, making sure to stare into James' eyes as she replied to Dean playfully, "I'm never too busy for you, _Dean_. You're my favorite."

"**Right**.." Dean cleared his throat at this, seemingly at a loss for words. He finally caught his breath, "**Well, I guess that's good news then. Your favorite's asking you for some help**."

Silk uncrossed her legs, sitting up with a bit more somberity to her movements now. "Help? You mean, with a case?"

She had only met Dean Winchester and his younger brother once, and that was at a fancy party about a month or so ago. The two brothers stood out in their clearly-rented-to-go suits, Dean's laid-back posture, and Sam's clearly over grown hair that swept across his forehead. In fact, Silk can remember crinkling her nose at the boys, instantly looking down at them at the moment she laid eyes on the two.

**- Rewind; one month ago**

_'They will let anyone into these things nowadays, huh?' _Silk could remember thinking to herself as she gave her wine glass a gentle twirl, a frown on her lips as she spotted two men who painfully stood out amongst the crowds of noble men and woman.

No one else seemed to notice the two sore thumbs in the room, but the brunette couldn't keep her eyes off of them. Well-, there was plenty of women who noticed the two men. Like birds in a flock, rich women after rich women threw theirselves at the two men subtly, but that wasn't why Silk couldn't tear her chocolate hues from the two.

No, these two boys amplified the aura of danger. Danger, danger, danger. There was no way she'd let either out of her sights.

Her interest was peaked, because maybe these two men were like her. Now, Silk in no sense was _pretending _to be of nobility as she mingled with the crowd at the party. She belonged with this rich crowd, drinking overly expensive wine and eating finger sandwhiches. Her gold cocktail dress was a name brand, never a knock off, and she could call a majority of the people at the party by their first name basis if she wished.

However, she wasn't here for merely expensive wine and cheese, and networking. And Silk had a strong feeling those two men weren't, either.

So, when she saw the taller one with the shaggy hair duck out the back into the hallway and leave the party, Silk knew it was time to quit watching, and act. She placed a hand on the man who currently had his arm wrapped around her waist and was showing her off like a golden trophy to another couple, and gently pushed him away.

The man, Charles, looked down at her in confusion. "Is something wrong, Cassandra dear?"

Silk gave him the prettiest, most innocent smile she could muster. "I've got to go powder my nose," She lied effortlessly. If the stupid dolt would just pay attention, he'd of been able to tell that the woman wasn't wearing a lick of makeup besides the mascara and red lipstick she'd painted onto her face.

But of course, Charles didn't notice her meager lie and let her slip from his grip without question. Heels clicking on the floor, Silk rushed off to follow the shaggy haired male, but not before checking over her shoulder to look at the shorter, more buff looking man. He seemed completely oblivious as he stuffed his mouth with as many finger sandwhiches his cheeks could hold, like a wild squirrel.

Silk scrunched her nose in disgust before following after the taller man.

The brunette had resulted in taking off her high heels and leaving them in a pot of roses out of any wandering eyes view. The clacking against marble would be far too obnoxious for her own sanity, and Silk knew herself to be more agile while bare-footed.

She reached into her gold clutch purse, her fingers clutching onto her taser. Not her exact weapon of choice, but for now it would do. Sneaking her taser in was a lot less hassle then sneaking in her two beloved pistols, Ivory and Ebony.

So with her taser drawed and ready in one hand, Silk glanced up at the hallway's chandelier as the lightbulbs began to flicker on and off. Well, she's been in situations creepier then this. The ballroom music could be heard faintly from the party, and Silk gave a weary glance behind her just to make sure no one followed her from out the party.

She could see her breath, and Silk instantly wondered when the rooms temperature dropped so low, but she didn't get the chance to ponder it when she felt a blow to her left temple, dropping her to the ground.

"Ugh-!"

She hit the marble floor hard, placing both her palms against the ground to take a moment and regain her focus. Silk managed to lift her head enough to peek from her eyelashes who her attacker was. The tall man with shaggy hair from the party stood in front of her, gun pointed down at her.

Well, shit.

The look in his eye was crazy, and Silk had no doubt he would pull the trigger. He glared down at her like she was some kind of monster and he had her right where he wanted her. Then she noticed the flicker on uncertainty in his eye, and the brunette immediately jumped into her acting skills.

Silk discreetly let go of her tazer inside of her purse so the crazy, gun-wielding maniac wouldn't notice, and raised her hands in surrender. "Please.." She begged with feign innocence, acting as though she were beyond frightened. "Please.. just let me go.."

It seemed to have the right affect on her attacker for he lowered his gun, regret plastered on his face as he let his guard down, opening his mouth to spew out some crap. Silk wasn't in the listening mood, for the minute he lowered his gun, her leg shot right up and kicked the object right out of his hand, not giving a damn that she had just flashed the man her under garments.

He was thrown off, taking a few steps back in shock from her sudden advantage over him. Silk didn't hesitate in grabbing her tazer, raising the voltage, and zapping the man right in his nuts. He crumbled to the floor in pain.

Before Silk had a chance to regain her composure, she felt a hard thump in the back of her head. Her eyes rolled back as she passed out, her mind silently cursing herself for forgetting about the mans partner before she hit the ground.

"Lookie, the evil son of a bitch is awakening." Silk clenched her eyes shut at the obnoxious males voice, her head ringing in pain from the strike to her temple before.

"Dean.. I don't know, she seems kind of.."

"Innocent?" Dean, Silk assumed that was his name, snapped back at the other man with annoyance. "Yeah, that's kind of what demons _do_, Sam."

"Yeah, I get that.." Sam sounded stressed and annoyed by his brothers eagerness. "But the thing is, I think she's just a normal civilian-"

"Then why did she attack, huh?" He shot back.

Their arguing was useless, Silk decided. Whatever the two lovebirds were bickering about, she really couldn't give a damn as long as they kept their attention off of her. She was tied up to a chair, her wrists tied behind her back, and her feet tied together as well. She shifted discreetly, realizing she could move her wrists just the slightest bit.

"You can't let her disguise fool you, Sammy." Dean said after an exhausted moment of arguing. "It's a pretty meatsuit, but the thing inside of her is not human."

"Excuse me?" Silk used her fingertips to tug at the hard rope, tearing some of it off her wrist piece by piece. She tried to remain natural, "But if anyone isn't human here, its you two. You guys are monsters."

They did, after all, attack a seemingly innocent young woman. If they weren't the monsters, Silk wasn't sure who would be.

"Look at the kettle calling the pot black," was Dean's smug response. Silk snarled at him, hacking in the back of her throat to spit green mucus at the man, successfully landing on his black shoes.

"How about you fuck off, buddy?" She growled at him. Dean looked down at his now dirty shoe in disgust, shooting Sam a look of disbelief before raising an eyebrow at the woman.

He dug into his pocket, pulling out a flask with water into it. Silk narrowed her eyes as he approached her, popping the lid of the silver flask off before sprinkling her with the water. Silk clutched her eyes shut instinctively as the water sprinkled onto her, expecting it to burn like acid and melt her skin off. After a moment of silence, she unclenched her eyes to reveal the two boys looking equally as confused.

Silk snorted, "You'll have to do better then that."

"Dean!" Sam snapped, sounding remorseful. The elder looked down to Silk with confusion, but his furrowed eyebrows showed he wasn't ready to give in just yet. The taller one held out his knife, taking a step towards Silk. "That's it, I'm letting her go, we have the wrong person-"

Unknown to the two boys, Silk had managed to claw her wrists free from the rope, and the instant Sam took a step towards her bearing his knife, she reacted immediately. Tugging the rope away from her torso, the brunette palmed Sam in the nose, causing him to recoil back with tears in his eyes, and dropped his knife.

The knife was already in Silk's hand and cutting the rope around her ankles, and she was back on her feet before Dean had the chance to tackle her back to the ground. She pointed the knife at him wearily, everyone now frozen as Silk's eyes darted from the man on the floor clutching his nose, to the man who stood in front of her with a dangerous look on his face.

Somehow she had managed to get the upper hand, but Silk wasn't sure she can handle both of the men at the same time. For some reason, Dean looked way too smug for someone who had a knife pointed at his neck, and Silk shot him a dirty look as she asked, "You find me about to slice your throat funny, fuck boy?"

"You're as harmful as a fly inside of that Devil's trap, bitch." He was speaking nonsense to Silk, yet he looked so confident doing so. Devil's trap? What the hell was this idiot talking about? Dean snapped his head to Sam, who was slowly standing up from the ground. "Do it, Sammy!"

Silk's eyes raised up to the ceiling, seeing a strange circle with a star inside of it. Is this what was supposed to keep her.. trapped? It was about time to give these boys a rain check.

As Sam opened his mouth and began to chant, Silk stepped out from the circle and swung her leg at Dean's ankles, knocking him to the floor. She was on him instantly, gold dress riding up her thighs as she straddled his waist, pinning him to the ground with her knife pointed at his neck. She was done playing, and Silk wasn't prepared to hesitate a bit as the knife pressed against the mans throat, ready to cut it open and bleed him to death.

A gust of wind, like a random window flew open and knocked her back, Silk soon found herself smashed against the wall with an immense amount of pressure keeping her dangling in the air. She was caught off guard by the sudden impact, and silently wondered how the hell either of the boys managed to pull something like this off.

That was, until she looked to the side and saw both Sam and Dean pressed against the wall with equal the confusion. She heard Sam sigh, "_Here's _the real demon."

"Someone should have told me the party was in here.."

Charles, Silk's date for the night, cut off their confusion as he stepped into the room. Something was different about him, inhumane looking that sent chills down the brunettes spine. The devil shifted his black eyes towards Silk, a filthy smile forming on his face. "You were taking a long time in the bathroom, love. Had to come check on you."

"I see you've brought back up, Charles. Bitch move on your part," It was a struggle for Silk to speak with the amount of gravity pressed against her stomach.

The demon laughed at her insult, "The Winchester are no friends of mine." He smirked, sending the two men a look of triumph with just a mere tilt of his head. He began to take a step closer, stepping onto a maroon rug that was at the center of the room, giving the demon a good look at his three new captives. "In fact, this was my plan all along.. The Winchester brothers and the Bitch, all in the same room.. all at my mercy."

Silk began to squirm a bit at this. The thought of being at _anyones _mercy made her a bit uneasy. Charles stepped away from the rug, approaching Silk as he stroked her cheek gingerly. The young woman swallowed hard, her glare never leaving his eyes.

"Leave the civilian alone," Dean tried to reason strongly with the demon, who tore his gaze away from Silk to shoot the elder Winchester a glare. Inwardly, Silk was grateful to have the demon- _Charles_, whoever the hell he was, attention off of her. "Let her go. You've got Sam and I."

Charles began to make his way over to Dean's side of the corner, 'tsk'ing loudly as he did so. "Now why would I do that?" He chuckled at the thought, "The little bitch has been waiting for a chance to kill me all night." Charles shot Silk a look over his shoulder, as if asking her to confirm it.

If Silk was thrown off, she didn't show it. She wasn't sure as to how Charles knew about her mission to assassinate him, in fact she had been certain the former convict was head over heels blinded by love with her just a few hours ago. She smirked at him, not wanting him to know that he had thrown her off.

"Yup, been waiting to cut that little throat of yours the moment you were off guard." She admitted shamelessly.

Charles chuckled as he stepped onto the rug, now approaching Dean. "I guess this meatsuit of mine wasn't a very good man in his life. Mans got some dangerous enemies."

Now, Silk couldn't believe this whole.. '_demons' _business. But there was currently no clear explanation as to how this monster in front of her was managing to hold her three feet in the air hostage, followed by the other two victims in the room. And if there was one thing she was sure of, this man was _not t_he Charles whom she had arrived at the ball with.

"That's rich, coming from a _demon_." Dean spat sarcastically.

"Let the girl go, she has nothing to do with this." Sam tried to reason from the other corner. Charles shot him a sadistic look, a grin showing his pointy canine teeth swept across his lips.

"You're right.. how about I kill the bitch first, so we can have our alone time boys?"

Silk's breath caught in her throat. Shit.

The demon crossed the carpet to approach Silk, but froze in his place. He looked up fearfully, "...Damn it."

Suddenly, the three captives dropped to the ground hard, and Silk took a moment to catch her breath. She watched as Sam and Dean charged immediately at the demon, Dean sprinkling him with the water stuff which seemed to literally burn the man. Silk watched, mouth wide as the two brother began to circle the trapped demon.

Dean smirked as he pointed to the carpet, "There's a devil trap underneath, you evil son of a bitch."

Silk had no idea why the demon Charles suddenly looked so angry, but the way the room began to shake and books fell from their shelves gave her the idea that he was incredibly _pissed_.

"That won't be good enough for me, boys." The demon said darkly as the floor cracked, breaking the devils seal. Silk was crawling away from the fight and out of view now, watching as the demon freed himself and shot Sam to the wall. Dean was next to get sent flying, and he hit the bookshelf so hard she could hear it crack in two.

"Now where's the Bitch-" Demon-Charles had no way of finishing his vulgar insult as Silk came from behind, recklessly prying the demons jaw open with her fingers as she shoved her taser down his throat, tazing him from the inside.

The boys dropped to the floor for the second time as both Dean and Sam began to cough the air back into their lungs, trying to regain their balance on two feet. Silk wasn't done yet though, as she watched Charles' body drop to the ground twitching and fried, she took her knife and dove it into his neck, sawing the bone in half until the head rolled decapitated from its body.

One monster down. Silk jumped like a frightened cat at the sound of wood creaking, whipping around to point the bloody knife at the two Winchester boys.

"Are you guys working with him?" She demanded harshly, confusing the two. Sam instantly raised his hands in the air to show her he was innocent, speaking to her quietly.

"There's been a misunderstanding.." Sam started slowly.

Silk cut him off, "Yeah, you fucking assholes tied me up as bait for Charles."

"If you couldn't tell, we were all pretty screwed their for a minute, lady." Dean replied with annoyance in his tone. Silk shot him a dark look, pointing her dagger at him as he continued. "We're all on the same side here."

She narrowed her eyes at the green eye'd Winchester, "You guys almost got me _killed_."

"Yeah, well it sounded like you were in a mess with or without our help." Dean shot back, taking a step towards the woman. He placed a hand on her wrist to gently lower the blade, "Just put the knife down before you hurt yourself.."

He snatched the knife from her hand quickly and Silk balled her hand into a fist, knocking him once in the nose, and then to the side of his temple, and kicked his ankles to knock him to the ground. She snatched the knife back from him, backing out of the door with the blade pointed at Sam, threatening to attack if he tried to stop her from retreating.

"That's for tying me up!" She snapped, before turning on her heel and running barefoot out the library before either can react.

She made sure to grab her shoes out of the potted plant before she left the party for good, silently fuming. Oh well, Charles was dead, demon or not. That meant she could go and get her reward.

**FIN**

**A/N; Here's chapter one! Chapter two will continue the flashback from a month ago, before returning back to Dean and Silk's phone call. I wonder which case Dean will be asking for Silk's help with? Reviews will make me update quickly.**


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